#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/02/7120204.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7120204
loop_
_publ_author_name
'Kontham, Ravindar'
'Kambale, Digambar Abasaheb'
'Thorat, Sagar Sudam'
'Pratapure, Madhukar Shivaji'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Lewis acid catalyzed cascade annulation of alkynols with α-ketoesters: A
 facile access to γ-spiroketal-γ-lactones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03668J
_journal_year                    2017
_chemical_formula_moiety         'C19 H22 O3'
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-17 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                93.6160(10)
_cell_angle_beta                 92.6120(10)
_cell_angle_gamma                93.620(2)
_cell_formula_units_Z            2
_cell_length_a                   6.4777(2)
_cell_length_b                   8.9647(2)
_cell_length_c                   13.3928(3)
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.42
_cell_measurement_theta_min      2.28
_cell_volume                     773.67(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10344
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.525
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0433P)²+0.4332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2502
_reflns_number_total             3006
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc03668j2.cif
_cod_data_source_block           msb_164_160616_0m
_cod_database_code               7120204
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.39126(18) 0.32530(12) 0.24699(8) 0.0180(3) Uani 1 1 d . .
O2 O 0.12618(17) 0.41337(13) 0.14733(8) 0.0177(3) Uani 1 1 d . .
O3 O -0.13935(17) 0.33879(13) 0.03984(9) 0.0228(3) Uani 1 1 d . .
C1 C 0.3477(2) 0.39104(18) 0.15670(12) 0.0159(4) Uani 1 1 d . .
C2 C 0.4709(3) 0.54146(18) 0.16454(12) 0.0181(4) Uani 1 1 d . .
H2A H 0.3964 0.6162 0.1282 0.022 Uiso 1 1 calc R U
H2B H 0.6085 0.5323 0.1363 0.022 Uiso 1 1 calc R U
C3 C 0.4936(3) 0.58775(18) 0.27812(12) 0.0164(4) Uani 1 1 d . .
C4 C 0.4144(3) 0.44307(18) 0.32537(12) 0.0199(4) Uani 1 1 d . .
H4A H 0.5147 0.4172 0.3785 0.024 Uiso 1 1 calc R U
H4B H 0.2798 0.4576 0.3555 0.024 Uiso 1 1 calc R U
C5 C 0.3593(3) 0.71740(19) 0.30657(12) 0.0207(4) Uani 1 1 d . .
H5A H 0.3966 0.8032 0.2664 0.025 Uiso 1 1 calc R U
H5B H 0.2119 0.6855 0.2899 0.025 Uiso 1 1 calc R U
C6 C 0.3859(3) 0.7679(2) 0.41781(13) 0.0252(4) Uani 1 1 d . .
H6A H 0.3018 0.8545 0.4319 0.030 Uiso 1 1 calc R U
H6B H 0.3353 0.6856 0.4581 0.030 Uiso 1 1 calc R U
C7 C 0.6122(3) 0.8119(2) 0.44814(14) 0.0287(4) Uani 1 1 d . .
H7A H 0.6262 0.8369 0.5213 0.034 Uiso 1 1 calc R U
H7B H 0.6576 0.9024 0.4141 0.034 Uiso 1 1 calc R U
C8 C 0.7511(3) 0.6858(2) 0.42075(13) 0.0260(4) Uani 1 1 d . .
H8A H 0.7193 0.6005 0.4623 0.031 Uiso 1 1 calc R U
H8B H 0.8977 0.7213 0.4357 0.031 Uiso 1 1 calc R U
C9 C 0.7208(3) 0.6328(2) 0.30989(12) 0.0206(4) Uani 1 1 d . .
H9A H 0.8048 0.5459 0.2964 0.025 Uiso 1 1 calc R U
H9B H 0.7718 0.7140 0.2688 0.025 Uiso 1 1 calc R U
C10 C 0.3810(2) 0.28441(18) 0.07030(12) 0.0156(3) Uani 1 1 d . .
H10 H 0.5111 0.2476 0.0552 0.019 Uiso 1 1 calc R U
C11 C 0.2047(2) 0.24697(17) 0.01657(12) 0.0153(3) Uani 1 1 d . .
C12 C 0.0408(3) 0.33274(18) 0.06492(12) 0.0168(4) Uani 1 1 d . .
C13 C 0.1712(2) 0.14152(17) -0.07234(12) 0.0149(3) Uani 1 1 d . .
C14 C 0.3385(3) 0.06692(18) -0.10993(12) 0.0176(4) Uani 1 1 d . .
H14 H 0.4724 0.0864 -0.0781 0.021 Uiso 1 1 calc R U
C15 C 0.3119(3) -0.03420(18) -0.19231(12) 0.0181(4) Uani 1 1 d . .
H15 H 0.4278 -0.0827 -0.2164 0.022 Uiso 1 1 calc R U
C16 C 0.1177(3) -0.06626(18) -0.24077(12) 0.0181(4) Uani 1 1 d . .
C17 C -0.0480(3) 0.00705(19) -0.20348(13) 0.0207(4) Uani 1 1 d . .
H17 H -0.1818 -0.0135 -0.2352 0.025 Uiso 1 1 calc R U
C18 C -0.0230(3) 0.10945(19) -0.12108(12) 0.0196(4) Uani 1 1 d . .
H18 H -0.1393 0.1582 -0.0976 0.023 Uiso 1 1 calc R U
C19 C 0.0894(3) -0.1782(2) -0.33000(13) 0.0260(4) Uani 1 1 d . .
H19A H 0.2213 -0.1855 -0.3625 0.039 Uiso 1 1 calc R U
H19B H -0.0148 -0.1455 -0.3777 0.039 Uiso 1 1 calc R U
H19C H 0.0435 -0.2765 -0.3078 0.039 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C4 107.70(12)
C12 O2 C1 109.50(12)
O1 C1 O2 109.08(12)
O1 C1 C10 110.12(13)
O2 C1 C10 103.63(12)
O1 C1 C2 105.83(13)
O2 C1 C2 109.90(13)
C10 C1 C2 118.11(13)
C1 C2 C3 105.16(13)
C1 C2 H2A 110.7
C3 C2 H2A 110.7
C1 C2 H2B 110.7
C3 C2 H2B 110.7
H2A C2 H2B 108.8
C5 C3 C9 109.46(14)
C5 C3 C4 110.59(13)
C9 C3 C4 111.97(13)
C5 C3 C2 111.79(13)
C9 C3 C2 110.53(13)
C4 C3 C2 102.37(13)
O1 C4 C3 107.58(12)
O1 C4 H4A 110.2
C3 C4 H4A 110.2
O1 C4 H4B 110.2
C3 C4 H4B 110.2
H4A C4 H4B 108.5
C6 C5 C3 112.34(14)
C6 C5 H5A 109.1
C3 C5 H5A 109.1
C6 C5 H5B 109.1
C3 C5 H5B 109.1
H5A C5 H5B 107.9
C7 C6 C5 111.14(15)
C7 C6 H6A 109.4
C5 C6 H6A 109.4
C7 C6 H6B 109.4
C5 C6 H6B 109.4
H6A C6 H6B 108.0
C6 C7 C8 111.48(15)
C6 C7 H7A 109.3
C8 C7 H7A 109.3
C6 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 108.0
C7 C8 C9 111.57(15)
C7 C8 H8A 109.3
C9 C8 H8A 109.3
C7 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
C8 C9 C3 112.80(14)
C8 C9 H9A 109.0
C3 C9 H9A 109.0
C8 C9 H9B 109.0
C3 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C1 111.36(14)
C11 C10 H10 124.3
C1 C10 H10 124.3
C10 C11 C13 128.10(15)
C10 C11 C12 106.55(14)
C13 C11 C12 125.35(14)
O3 C12 O2 121.21(15)
O3 C12 C11 129.85(15)
O2 C12 C11 108.92(13)
C18 C13 C14 117.64(15)
C18 C13 C11 122.62(15)
C14 C13 C11 119.73(14)
C15 C14 C13 121.19(15)
C15 C14 H14 119.4
C13 C14 H14 119.4
C14 C15 C16 121.08(15)
C14 C15 H15 119.5
C16 C15 H15 119.5
C17 C16 C15 117.78(15)
C17 C16 C19 121.48(15)
C15 C16 C19 120.74(15)
C18 C17 C16 121.71(15)
C18 C17 H17 119.1
C16 C17 H17 119.1
C17 C18 C13 120.60(15)
C17 C18 H18 119.7
C13 C18 H18 119.7
C16 C19 H19A 109.5
C16 C19 H19B 109.5
H19A C19 H19B 109.5
C16 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4032(19)
O1 C4 1.4370(19)
O2 C12 1.357(2)
O2 C1 1.4622(19)
O3 C12 1.205(2)
C1 C10 1.486(2)
C1 C2 1.518(2)
C2 C3 1.549(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C5 1.535(2)
C3 C9 1.535(2)
C3 C4 1.548(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.528(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.523(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.527(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.530(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.334(2)
C10 H10 0.9500
C11 C13 1.472(2)
C11 C12 1.497(2)
C13 C18 1.396(2)
C13 C14 1.405(2)
C14 C15 1.380(2)
C14 H14 0.9500
C15 C16 1.394(2)
C15 H15 0.9500
C16 C17 1.389(2)
C16 C19 1.508(2)
C17 C18 1.387(2)
C17 H17 0.9500
C18 H18 0.9500
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O1 C1 O2 -82.97(14)
C4 O1 C1 C10 163.94(13)
C4 O1 C1 C2 35.22(16)
C12 O2 C1 O1 -118.38(14)
C12 O2 C1 C10 -1.10(15)
C12 O2 C1 C2 126.01(14)
O1 C1 C2 C3 -27.74(16)
O2 C1 C2 C3 89.91(14)
C10 C1 C2 C3 -151.57(14)
C1 C2 C3 C5 -108.21(15)
C1 C2 C3 C9 129.60(14)
C1 C2 C3 C4 10.18(16)
C1 O1 C4 C3 -28.63(16)
C5 C3 C4 O1 129.28(14)
C9 C3 C4 O1 -108.35(15)
C2 C3 C4 O1 10.05(16)
C9 C3 C5 C6 -55.17(18)
C4 C3 C5 C6 68.65(18)
C2 C3 C5 C6 -177.98(14)
C3 C5 C6 C7 56.39(19)
C5 C6 C7 C8 -54.8(2)
C6 C7 C8 C9 53.8(2)
C7 C8 C9 C3 -54.2(2)
C5 C3 C9 C8 54.10(18)
C4 C3 C9 C8 -68.90(18)
C2 C3 C9 C8 177.66(14)
O1 C1 C10 C11 116.30(15)
O2 C1 C10 C11 -0.25(17)
C2 C1 C10 C11 -122.03(16)
C1 C10 C11 C13 -178.00(14)
C1 C10 C11 C12 1.36(17)
C1 O2 C12 O3 -176.92(14)
C1 O2 C12 C11 1.94(16)
C10 C11 C12 O3 176.65(17)
C13 C11 C12 O3 -4.0(3)
C10 C11 C12 O2 -2.08(17)
C13 C11 C12 O2 177.31(14)
C10 C11 C13 C18 178.67(16)
C12 C11 C13 C18 -0.6(2)
C10 C11 C13 C14 -0.2(2)
C12 C11 C13 C14 -179.44(14)
C18 C13 C14 C15 0.2(2)
C11 C13 C14 C15 179.09(14)
C13 C14 C15 C16 -0.3(2)
C14 C15 C16 C17 0.1(2)
C14 C15 C16 C19 -179.29(15)
C15 C16 C17 C18 0.3(2)
C19 C16 C17 C18 179.61(16)
C16 C17 C18 C13 -0.4(3)
C14 C13 C18 C17 0.1(2)
C11 C13 C18 C17 -178.74(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187764
